Why B-ring is the active center for genistein to scavenge peroxyl radical: A DFT study

Bioorganic and Medicinal Chemistry Letters

Volumn 13, Issue 5, 2003, Pages 909-911

  Zhang, Hong Yu ^a   Wang, Lan Fen ^b   Sun, You Min ^c  

^a SHANDONG UNIVERSITY OF TECHNOLOGY   (China)

^b SHANDONG NORMAL UNIVERSITY   (China)

^c SHANDONG UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

GENISTEIN; PEROXY RADICAL; PYRONE DERIVATIVE; SCAVENGER;

ARTICLE; CALCULATION; CONJUGATION; DENSITY; ELECTRON; STRUCTURE ACTIVITY RELATION;

EID: 0037430551     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(03)00013-1     Document Type: Article

References (51)

1. (a) Bors W., Hetter W., Michel C., Saran M. Methods Enzymol. 186:1990;343
2. (b) Jovanovic S.V., Steenken S., Tosic M., Marjanovic B., Simic M.G. J. Am. Chem. Soc. 116:1994;4846
3. (c) Jovanovic S.V., Steenken S., Hara Y., Simic M.G. J. Chem. Soc., Perkin Trans. 2. 11:1996;2497
4. (d) Roginsky V.A., Barsukova T.K., Remorova A.A., Bors W. J. Am. Oil Chem. Soc. 73:1996;777
5. (e) Foti M., Piattelli M., Baratta M.T., Ruberto G. J. Agric. Food. Chem. 44:1996;497
6. (f) Rice-Evans C.A., Miller N.J., Paganga G. Free Radic. Biol. Med. 20:1996;933
7. (g) Ogata M., Hoshi M., Shimotohno K., Urano S., Endo T. J. Am. Oil Chem. Soc. 74:1997;557
8. (h) Bors W., Michel C. Biofactors. 6:1997;399
9. (i) Arora A., Nair M.G., Strasburg G.M. Free Radic. Biol. Med. 24:1998;1355
10. (j) Croft K.D., Ann N.Y. Acad. Sci. 854:1998;435 (k) Pietta P.-G. J. Nat. Prod. 63:2000;1035.
11. (a) Bors W., Hetter W., Michel C., Saran M. Methods Enzymol. 186:1990;343 (b) Jovanovic S.V., Steenken S., Tosic M., Marjanovic B., Simic M.G. J. Am. Chem. Soc. 116:1994;4846 (c) Jovanovic S.V., Steenken S., Hara Y., Simic M.G. J. Chem. Soc., Perkin Trans. 2. 11:1996;2497 (d) Roginsky V.A., Barsukova T.K., Remorova A.A., Bors W. J. Am. Oil Chem. Soc. 73:1996;777 (e) Foti M., Piattelli M., Baratta M.T., Ruberto G. J. Agric. Food. Chem. 44:1996;497 (f) Rice-Evans C.A., Miller N.J., Paganga G. Free Radic. Biol. Med. 20:1996;933 (g) Ogata M., Hoshi M., Shimotohno K., Urano S., Endo T. J. Am. Oil Chem. Soc. 74:1997;557 (h) Bors W., Michel C. Biofactors. 6:1997;399 (i) Arora A., Nair M.G., Strasburg G.M. Free Radic. Biol. Med. 24:1998;1355 (j) Croft K.D., Ann N.Y. Acad. Sci. 854:1998;435 (k) Pietta P.-G. J. Nat. Prod. 63:2000;1035.
12. (a) Arora A., Nair M.G., Strasburg G.M. Arch. Biochem. Biophys. 356:1998;133
13. (a) Arora A., Nair M.G., Strasburg G.M. Arch. Biochem. Biophys. 356:1998;133 (b) Arora A., Valcic S., Cornejo S., Nair M.G., Timmermann B.N., Liebler D.C. Chem. Res. Toxicol. 13:2000;638.
14. (a) Zhang H.Y. Sci. China (ser B). 42:1999;106
15. (b) Hino F., Eriksson L.A., Blomberg M.R.A., Siegbahn P.E.M. Int. J. Quantum Chem. 76:2000;714
16. (c) Wright J.S., Johnson E.R., DiLabio G.A. J. Am. Chem. Soc. 123:2001;1173
17. (a) Zhang H.Y. Sci. China (ser B). 42:1999;106 (b) Hino F., Eriksson L.A., Blomberg M.R.A., Siegbahn P.E.M. Int. J. Quantum Chem. 76:2000;714 (c) Wright J.S., Johnson E.R., DiLabio G.A. J. Am. Chem. Soc. 123:2001;1173 (d) Zhang H.Y., Sun Y.M., Wang X.L. Chem-Eur. J. 9:2003;502.
18. (a) de Heer M.I., Korth H.-G., Mulder P. J. Org. Chem. 64:1999;6969
19. (b) Bakalbassis E.G., Chatzopoulou A., Melissas V.S., Tsimidou M., Tsolaki M., Vafiadis A. Lipids. 36:2001;181
20. (c) Pratt D.A., DiLabio G.A., Brigati G., Pedulli G.F., Valgimigli L. J. Am. Chem. Soc. 123:2001;4625
21. (d) Zhang H.Y. J. Am. Oil. Chem. Soc. 76:1999;745
22. (e) Zhang H.Y. Quant. Struct.-Act. Relat. 19:2000;50
23. (f) Sun Y.M., Wang X.L., Zhang H.Y., Chen D.Z. Quant. Struct.-Act. Relat. 20:2001;139
24. (g) Zhang H.Y., Wang L.F. Bioorg. Med. Chem. Lett. 12:2002;225
25. (a) de Heer M.I., Korth H.-G., Mulder P. J. Org. Chem. 64:1999;6969 (b) Bakalbassis E.G., Chatzopoulou A., Melissas V.S., Tsimidou M., Tsolaki M., Vafiadis A. Lipids. 36:2001;181 (c) Pratt D.A., DiLabio G.A., Brigati G., Pedulli G.F., Valgimigli L. J. Am. Chem. Soc. 123:2001;4625 (d) Zhang H.Y. J. Am. Oil. Chem. Soc. 76:1999;745 (e) Zhang H.Y. Quant. Struct.-Act. Relat. 19:2000;50 (f) Sun Y.M., Wang X.L., Zhang H.Y., Chen D.Z. Quant. Struct.-Act. Relat. 20:2001;139 (g) Zhang H.Y., Wang L.F. Bioorg. Med. Chem. Lett. 12:2002;225 (h) Sun Y.M., Zhang H.Y., Chen D.Z., Liu C.B. Org. Lett. 4:2002;2909.
26. (a) Wu Y.D., Lai D.K.W. J. Org. Chem. 61:1996;7904
27. (b) Wright J.S., Carpenter D.J., McKay D.J., Ingold K.U. J. Am. Chem. Soc. 119:1997;4245
28. (c) DiLabio G.A., Pratt D.A., LoFaro A.D., Wright J.S. J. Phys. Chem. A. 103:1999;1653
29. (d) Brinck T., Haeberline M., Jonsson M. J. Am. Chem. Soc. 119:1997;4239
30. (e) Brinck T., Lee H.-N., Jonsson M. J. Phys. Chem. A. 103:1999;7094
31. (f) DiLabio G.A., Pratt D.A., Wright J.S. Chem. Phys. Lett. 311:1999;215
32. (g) DiLabio G.A., Pratt D.A., Wright J.S. J. Org. Chem. 65:2000;2195
33. (a) Wu Y.D., Lai D.K.W. J. Org. Chem. 61:1996;7904 (b) Wright J.S., Carpenter D.J., McKay D.J., Ingold K.U. J. Am. Chem. Soc. 119:1997;4245 (c) DiLabio G.A., Pratt D.A., LoFaro A.D., Wright J.S. J. Phys. Chem. A. 103:1999;1653 (d) Brinck T., Haeberline M., Jonsson M. J. Am. Chem. Soc. 119:1997;4239 (e) Brinck T., Lee H.-N., Jonsson M. J. Phys. Chem. A. 103:1999;7094 (f) DiLabio G.A., Pratt D.A., Wright J.S. Chem. Phys. Lett. 311:1999;215 (g) DiLabio G.A., Pratt D.A., Wright J.S. J. Org. Chem. 65:2000;2195 (h) Zhang H.Y., Sun Y.M., Chen D.Z. Quant. Struct.-Act. Relat. 20:2001;148.
34. Gajewski J.J., Gilbert K.E., McKelvey J. Adv. Mol. Model. 2:1990;65.
35. Dewar M.J.S., Zoebisch E.G., Healy E.F., Stewart J.J.P. J. Am. Chem. Soc. 107:1985;3902.
36. Scott A.P., Radom L. J. Phys. Chem. 100:1996;16502.
37. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian 94, Revision E.3; Gaussian: Pittsburgh, PA, 1995.
38. (a) Tanaka K., Sakai S., Tomiyama S., Nishiyama T., Yamada F. Bull. Chem. Soc. Jpn. 64:1991;2677
39. (b) Tomiyama S., Sakai S., Nishiyama T., Yamada F. Bull. Chem. Soc. Jpn. 66:1993;299
40. (c) van Acker S.A.B.E., Koymans L.M.H., Bast A. Free Radic. Biol. Med. 15:1993;311
41. (d) Migliavacca E., Carrupt P.A., Testa B. Helv. Chim. Acta. 80:1997;1613
42. (e) Zhang H.Y. J. Am. Oil Chem. Soc. 75:1998;1705
43. (f) Zhang H.Y., Sun Y.M., Zhang G.Q., Chen D.Z. Quant. Struct.-Act. Relatsh. 19:2000;375
44. (a) Tanaka K., Sakai S., Tomiyama S., Nishiyama T., Yamada F. Bull. Chem. Soc. Jpn. 64:1991;2677 (b) Tomiyama S., Sakai S., Nishiyama T., Yamada F. Bull. Chem. Soc. Jpn. 66:1993;299 (c) van Acker S.A.B.E., Koymans L.M.H., Bast A. Free Radic. Biol. Med. 15:1993;311 (d) Migliavacca E., Carrupt P.A., Testa B. Helv. Chim. Acta. 80:1997;1613 (e) Zhang H.Y. J. Am. Oil Chem. Soc. 75:1998;1705 (f) Zhang H.Y., Sun Y.M., Zhang G.Q., Chen D.Z. Quant. Struct.-Act. Relatsh. 19:2000;375 (g) Foti M.C., Johnson E.R., Vinqvist M.R., Wright J.S., Barclay L.R.C., Ingold K.U. J. Org. Chem. 67:2002;5190.
45. Zhang H.Y., Sun Y.M., Wang X.L. J. Org. Chem. 67:2002;2709.
46. The intramolecular hydrogen bond between 5-OH and 4-oxo also results in the high O-H BDE (5) in 3.
47. The higher O-H PDE (5) in 3 than that in 2 stems from the intramolecular hydrogen bond between 5-OH and 4-oxo.
48. 3d.
49. 3d.
50. Lucarini M., Mugnaini V., Pedulli G.F. J. Org. Chem. 67:2002;928.
51. Liang, X. F.; Hu, T. X.; Han, C. In Proceedings of 4th Symposium on Free Radical Biology and Medicine, Yantai, China, 2001, p 31.